ZA200202231B - Substituted pyrroles as antiproliferative agents for the treatment of cancer. - Google Patents
Substituted pyrroles as antiproliferative agents for the treatment of cancer. Download PDFInfo
- Publication number
- ZA200202231B ZA200202231B ZA200202231A ZA200202231A ZA200202231B ZA 200202231 B ZA200202231 B ZA 200202231B ZA 200202231 A ZA200202231 A ZA 200202231A ZA 200202231 A ZA200202231 A ZA 200202231A ZA 200202231 B ZA200202231 B ZA 200202231B
- Authority
- ZA
- South Africa
- Prior art keywords
- methyl
- indol
- nitro
- dihydro
- dioxo
- Prior art date
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- 206010028980 Neoplasm Diseases 0.000 title claims description 22
- 201000011510 cancer Diseases 0.000 title claims description 15
- 230000001028 anti-proliverative effect Effects 0.000 title description 7
- 150000003233 pyrroles Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 107
- 239000000203 mixture Substances 0.000 claims description 57
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- 125000000217 alkyl group Chemical group 0.000 claims description 30
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 28
- 229920001223 polyethylene glycol Polymers 0.000 claims description 28
- -1 OPOsR'R? Chemical group 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 26
- 239000002202 Polyethylene glycol Substances 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 24
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- 239000011734 sodium Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- 229910052708 sodium Inorganic materials 0.000 claims description 16
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- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- FUOOLUPWFVMBKG-UHFFFAOYSA-N 2-Aminoisobutyric acid Chemical compound CC(C)(N)C(O)=O FUOOLUPWFVMBKG-UHFFFAOYSA-N 0.000 claims description 8
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
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- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- CAEWJEXPFKNBQL-UHFFFAOYSA-N prop-2-enyl carbonochloridate Chemical compound ClC(=O)OCC=C CAEWJEXPFKNBQL-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
- 229960002218 sodium chlorite Drugs 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000012178 vegetable wax Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15886099P | 1999-10-12 | 1999-10-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200202231B true ZA200202231B (en) | 2003-06-19 |
Family
ID=22570037
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200202231A ZA200202231B (en) | 1999-10-12 | 2002-03-19 | Substituted pyrroles as antiproliferative agents for the treatment of cancer. |
Country Status (30)
| Country | Link |
|---|---|
| EP (1) | EP1224181B1 (es) |
| JP (1) | JP2003511449A (es) |
| KR (1) | KR20020038817A (es) |
| CN (1) | CN1155595C (es) |
| AR (1) | AR026004A1 (es) |
| AT (1) | ATE255576T1 (es) |
| AU (1) | AU781732B2 (es) |
| BR (1) | BR0014680A (es) |
| CA (1) | CA2385071A1 (es) |
| CZ (1) | CZ20021610A3 (es) |
| DE (1) | DE60006990T2 (es) |
| DK (1) | DK1224181T3 (es) |
| ES (1) | ES2210005T3 (es) |
| HK (1) | HK1050533A1 (es) |
| HR (1) | HRP20020262B1 (es) |
| HU (1) | HUP0203558A3 (es) |
| IL (1) | IL148815A0 (es) |
| MA (1) | MA26830A1 (es) |
| MX (1) | MXPA02003667A (es) |
| NO (1) | NO20021718L (es) |
| NZ (1) | NZ518038A (es) |
| PE (1) | PE20010695A1 (es) |
| PL (1) | PL357441A1 (es) |
| PT (1) | PT1224181E (es) |
| RU (1) | RU2002110111A (es) |
| TR (1) | TR200200987T2 (es) |
| TW (1) | TWI230708B (es) |
| WO (1) | WO2001027106A1 (es) |
| YU (1) | YU25202A (es) |
| ZA (1) | ZA200202231B (es) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6313143B1 (en) * | 1999-12-16 | 2001-11-06 | Hoffmann-La Roche Inc. | Substituted pyrroles |
| US7776855B2 (en) | 2006-07-27 | 2010-08-17 | Janssen Pharmaceutica N.V. | Antimicrobial oxazolidinone prodrugs |
| WO2010151711A1 (en) * | 2009-06-25 | 2010-12-29 | Alkermes, Inc. | Prodrugs of nh-acidic compounds |
| UY34072A (es) | 2011-05-17 | 2013-01-03 | Novartis Ag | Derivados sustituidos de indol |
| CA2888194A1 (en) | 2012-11-07 | 2014-05-15 | Novartis Ag | Substituted indole derivatives |
| EP3771711A1 (en) | 2019-07-29 | 2021-02-03 | Bayer Animal Health GmbH | Pyrazole derivatives for controlling arthropods |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4005969A1 (de) * | 1990-02-26 | 1991-08-29 | Boehringer Mannheim Gmbh | Neue trisubstituierte pyrrole, verfahren zu ihrer herstellung sowie arzneimittel, die diese verbindungen enthalten |
| PE91598A1 (es) * | 1996-07-29 | 1998-12-24 | Hoffmann La Roche | Pirroles sustituidos |
| CZ299068B6 (cs) * | 1998-03-17 | 2008-04-16 | F. Hoffmann-La Roche Ag | Substituovaný bisindolylmaleinimid a farmaceutický prostredek s jeho obsahem |
-
2000
- 2000-10-02 PL PL00357441A patent/PL357441A1/xx not_active Application Discontinuation
- 2000-10-02 HU HU0203558A patent/HUP0203558A3/hu unknown
- 2000-10-02 RU RU2002110111/04A patent/RU2002110111A/ru not_active Application Discontinuation
- 2000-10-02 TR TR2002/00987T patent/TR200200987T2/xx unknown
- 2000-10-02 KR KR1020027004642A patent/KR20020038817A/ko not_active Application Discontinuation
- 2000-10-02 YU YU25202A patent/YU25202A/sh unknown
- 2000-10-02 CA CA002385071A patent/CA2385071A1/en not_active Abandoned
- 2000-10-02 JP JP2001530324A patent/JP2003511449A/ja active Pending
- 2000-10-02 AU AU79116/00A patent/AU781732B2/en not_active Ceased
- 2000-10-02 IL IL14881500A patent/IL148815A0/xx unknown
- 2000-10-02 ES ES00969381T patent/ES2210005T3/es not_active Expired - Lifetime
- 2000-10-02 WO PCT/EP2000/009635 patent/WO2001027106A1/en active IP Right Grant
- 2000-10-02 NZ NZ518038A patent/NZ518038A/en unknown
- 2000-10-02 CZ CZ20021610A patent/CZ20021610A3/cs unknown
- 2000-10-02 EP EP00969381A patent/EP1224181B1/en not_active Expired - Lifetime
- 2000-10-02 CN CNB008139857A patent/CN1155595C/zh not_active Expired - Fee Related
- 2000-10-02 BR BR0014680-3A patent/BR0014680A/pt not_active IP Right Cessation
- 2000-10-02 DK DK00969381T patent/DK1224181T3/da active
- 2000-10-02 MX MXPA02003667A patent/MXPA02003667A/es not_active Application Discontinuation
- 2000-10-02 AT AT00969381T patent/ATE255576T1/de not_active IP Right Cessation
- 2000-10-02 DE DE60006990T patent/DE60006990T2/de not_active Expired - Fee Related
- 2000-10-02 PT PT00969381T patent/PT1224181E/pt unknown
- 2000-10-06 PE PE2000001072A patent/PE20010695A1/es not_active Application Discontinuation
- 2000-10-11 TW TW089121145A patent/TWI230708B/zh not_active IP Right Cessation
- 2000-10-13 AR ARP000105331A patent/AR026004A1/es not_active Application Discontinuation
-
2002
- 2002-03-19 ZA ZA200202231A patent/ZA200202231B/en unknown
- 2002-03-27 HR HR20020262A patent/HRP20020262B1/xx not_active IP Right Cessation
- 2002-04-10 MA MA26592A patent/MA26830A1/fr unknown
- 2002-04-11 NO NO20021718A patent/NO20021718L/no not_active Application Discontinuation
-
2003
- 2003-04-16 HK HK03102759A patent/HK1050533A1/xx not_active IP Right Cessation
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